@article{SchmidtBergerKellingetal.2011, author = {Schmidt, Bernd and Berger, Ren{\´e} and Kelling, Alexandra and Schilde, Uwe}, title = {Pd-Catalyzed [2+2+1] coupling of alkynes and arenes phenol diazonium salts as mechanistic trapdoors}, series = {Chemistry - a European journal}, volume = {17}, journal = {Chemistry - a European journal}, number = {25}, publisher = {Wiley-Blackwell}, address = {Malden}, issn = {0947-6539}, doi = {10.1002/chem.201100609}, pages = {7032 -- 7040}, year = {2011}, abstract = {Alkynes and phenol diazonium salts undergo a Pd-catalyzed [2+2+1] cyclization reaction to spiro[4,5]decatetraene-7-ones. This structure was confirmed for one example by X-ray single-crystal structure analysis. The reaction is believed to proceed through oxidative addition of the phenol diazonium cation to Pd(0), subsequent insertion of two alkynes, followed by irreversible spirocyclization.}, language = {en} } @article{SchmidtBerger2013, author = {Schmidt, Bernd and Berger, Ren{\´e}}, title = {A deacetylation-diazotation-coupling sequence - palladium-catalyzed CC bond formation with acetanilides as formal leaving groups}, series = {Advanced synthesis \& catalysis}, volume = {355}, journal = {Advanced synthesis \& catalysis}, number = {2-3}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1615-4150}, doi = {10.1002/adsc.201200929}, pages = {463 -- 476}, year = {2013}, abstract = {Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross-coupling reactions, and a Pd-catalyzed [2+2+1]cycloaddition have been investigated as terminating CC bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal of by-products between the individual steps, but proceeds by addition of reagents and catalysts in due course.}, language = {en} } @article{SchmidtElizarovBergeretal.2013, author = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and Petersen, Monib H.}, title = {From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction}, series = {Synthesis}, volume = {45}, journal = {Synthesis}, number = {9}, publisher = {Thieme}, address = {Stuttgart}, issn = {0039-7881}, doi = {10.1055/s-0032-1316874}, pages = {1174 -- 1180}, year = {2013}, abstract = {A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization.}, language = {en} }